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NATIONAL ACADEMY of SCIENCES Volume 31 December 15

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NATIONAL ACADEMY of SCIENCES Volume 31 December 15 PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES Volume 31 December 15. 1945 Number 12 Copyright 1946 by the National Academy of Sciences THE SYNTHESIS OF BUTYRIC AND CAPROIC ACIDS FROM ETHANOL AND ACETIC ACID BY CLOSTRIDIUM KLUYVERI By H. A. BARKER, M. D. KAMEN* AND B. T. BORNSTEIN DIVISION OF PLANT NUTRITION, UNIVERSITY OF CALIFORNIA Communicated October 29, 1945 Unpublished investigations in this labora.tory have shown that Clostrid- ium kluyveri can metabolize acetic acid and ethanol under anaerobic con- ditions producing butyric and caproic acids in accordance with equations (1) and (2). CH3CH20H + CH3COOH = CH3CH2CH2COOH + H20 (1) 2CH3CH20H + CH3COOH = CH3(CH2)4COOH + 2H20 (2) The relative yields of the two acids are determined by the relative amounts of acetic acid and ethanol available. If acetic acid is present in excess, a considerable amount of butyric acid is formed, while if ethanol is in excess, caproic acid is the main product. These relations suggest that butyric acid may be an intermediate in the synthesis of caproic acid from acetic acid. This is supported by the observation that ethanol and butyric acid can be converted to caproic acid according to equation (3). CH3CH2OH + CH3CH2CH2COOH = CH3(CH2)4COOH + H20 (3) In the present investigation we have obtained positive proof for the con- version of acetic acid to caproic acid via butyric acid by studying the action of Cl. kluyveri on media containing synthetic fatty acids labeled with the long-lived radioactive carbon isotope C14. In addition we have obtained various types of evidence which help to elucidate the mechanism of fatty acid synthesis from C2 molecules. Experimental Methods.'-Carboxyl-labeled acetic, butyric and caproic acids were prepared from C*02 and methyl iodide, propyl bromide and amyl bromide, respectively, by the Grignard synthesis.1 The general technique of estimating the C14 content of carbon dioxide and fatty acids has already been described elsewhere.2 The barium salts Downloaded by guest on September 25, 2021 374 BA CTERIOLOG Y: BARKER, ET AL. PROC. N. A. S. of the fatty acids dried at 100°C. were used in the radio-assay. The indi- vidual acids were separated from mixtures by the distillation procedure of Schicktanz, et al,' The purity of each acid was established by Duclaux distillation. The methods used in locating C'4 in the individual carbon atoms of acetic and butyric acids have been described previously.2' 4, 5 The occurrence of C14 in the carboxyl group of caproic acid was deter- mined by decarboxylating the barium salt. Control experiments with syn- thetic caproic acid showed that this method yields 52 per cent of the. car- boxyl carbon as barium carbonate. The bacteria were grown in media of the following composition in g. per 100 ml.: ethanol 0.3-0.8, sodium salt of labeled acetic or butyric acid 0.3-0.6, yeast autolysate 0.3, pH 7.2, phosphate buffer M/40, (NH4)2SO4 0.1, MgSO4-7H200.01, FeSO4.7H20 0.0001, sodium thioglycollate 0.05, TABLE 1 THE FERMENTATION OF CH3CH2OH AND CH3C*OOH BY Cl. kluyveri Experiment 1 COMPOUND MM CTS./MIN./MM TOTAL CT$./MIN. Before growth Ethanol ca. 1. 1 .... Acetic acid ' 0.830 18,900 300 15,700 Carbon dioxide ca. 0.2 .... After growth Acetic acid 0.395 7330 150 2895 Butyric acid 0.196 18,200 300 3570 Caproic acid 0.257 24,500 500 6300 Carbon dioxide 0.185 26 50 5 Ethanol 0.217 260 = 50 74 Non-volatile cpds. 193 Percentage recovery of C'4.......................................... 83 traces of salts of Ca, Mn and Mo, distilled water. In some experiments sodium carbonate (0.025 g. per 100 ml.) was added as a sterile solution after autoclaving the medium. Oxygen was removed by means of either a pyrogallol-potassium carbonate or an Oxsorbent seal. The cultures were incubated at 32-35° until growth ceased before being analyzed. Results.-When Cl. kluyveri was allowed to grow in a medium containing approximately equivalent amounts of ethanol and synthetic carboxyl- labeled sodium acetate, radioactive butyric and caproic acids were formed (table 1). The isotope was proved to be present in these acids, rather' than in some associated compound, by establishing the constancy of the specific activities of the barium salts prepared from different fractions of a Duclaux distillation (table 2). A little C14 was also found in ethanol and unidenti- fied non-volatile compounds, but no significant amount was present in carbon dioxide. .It should be noted that there is no net production of Downloaded by guest on September 25, 2021 VOL. 31, 1945 BACTERIOLOGY: BARKER, ETAL. 375 carbon dioxide in thit fermentation. The recovery of C14 in all forms after growth was about 83 per cent of that initially added as acetic acid. A particularly significant fact revealed by this experiment is the de- crease in the molar activity of acetic acid during the fermentation. At the beginning of the experiment the activity expressed in cts./min./mM was 18.9 X 103 while at the end the value was 7.3 X 103. The simplest and most likely explanation for this reduction in activity is the oxidation of ethanol to inactive acetic acid or some closely related compound in equi- librium with it. This would cause a dilution of the labeled acetic acid. TABLE 2 SPECIFIC ACTIVITIES OF BARIUM SALTS OF BUTYRIC AND CAPROIC ACIDS PREPARED FROM DUCLAUx DISTILLATIONS Experiment 1 (total volume = 110 ml.) FRACTION CTS./MIN./MG. OF Ba SALT Butyric acid 0-20 ml. 47.5 20-40 ml. 47.6 40-110 ml. 46.4 Caproic acid 0-20 ml. 63.7 20-110 ml. 62.2 Another possible explanation for the decrease in activity of acetic acid is that it is in chemical and isotopic equilibrium with the higher fatty acids formed from it and ethanol. This was tested by two experiments in one of which butyric acid labeled in the carboxyl group was added at the be- ginning of the fermentation; in the second experiment butyric acid labeled on all four carbon atoms was used. In the experiment with carboxyl- labeled butyric acid (table 4), no C14 could be detected in the final acetic acid, thus indicating that no exchange occurred between the carboxyl groups of butyric acid and acetic acid. In the second experiment with com- pletely labeled butyric acid, a little C14 was recovered in the final acetic acid but it was less than 9 per cent of the amount to be expected if butyric and acetic acids were in isotopic equilibrium, and even this small effect may have been due to a slight contamination of the original butyric acid by labeled acetic acid. An exchange of C'4 between acetic acid and the higher fatty acids can therefore be excluded as an explanation for the observed decrease in activity of acetic acid. A third possible explanation for this effect is an exchange of C14 between ethanol and acetic acid as a result of reactions involving acetaldehyde or a similar compound as an intermediate. If such a reaction occurs, the residual ethanol should have the same molar activity as the acetic acid. Actually, the activity of the alcohol is of a lower order of magnitude Downloaded by guest on September 25, 2021 376 BA CTERIOLOG Y: BARKER, ET AL. PROC. N4. A. S. (table 1). Therefore an exchange of C14 between acetic acid and ethanol is not consistent with the observed results. Whatever the actual mechanism of the dilution of the active acetic acid, the magnitude of the effect is about what would be expected if all the ethanol is oxidized to acetic acid while the latter is being converted to higher fatty acids. To calculate the expected decrease of acetic acid activity on this basis, let us assume that (1) the fermentation proceeds in two successive steps represented by equations (1) and (3), and that during the fermentation all the ethanol is first converted to acetic acid or some compound in isotopic equilibrium with it. In step 1, the formation of butyric acid from ethanol and acetic acid, let x = the amount of C14 present in acetic acid at any time, xo = the initial C14, x, = the C14 at the end of step 1, V = the amount of acetic acid present at any time, Vo = the initial acetic acid, and Vf = the final acetic acid. Now during step 1, when a small amount (AV) of alcohol is oxidized to inactive acetic acid, the re- moval of active acetic acid by conversion to butyric acid will be equal to 2 A V. The loss of C14 fromi acetic acid is therefore -AX = -2AV/V- AV-x. (4) In the limit as A V approaches zero dxlx = 2d V/V. (4a) Integrating between the limits of VO and V,, and xo and xi and changing to log,o we get log xl/xO = 2 log Vf/ Vo (5) or Xi = Xo(V/ o) 2. (5a) In step 2 (equation 3), the conversion of alcohol and butyric acid to 'caproic acid, there is no change in the total quantity of acetic acid; V, is therefore a constant. C14 will nevertheless be lost from acetic acid if, as is assumed, it is an intermediate in the utilization of ethanol. When a small amount of alcohol (AA) is used, the loss of C14 from acetic acid is -Ax = AA/(V, + 4A)*x. (6) In the limit -dx/x = dA/Vf. (6a) Integrating between the limits xi and xf, and 0 and A,, where A, is the total amount of alcohol used in step 2 ln xl/xf = 2.3 log xl/xf = A,/ Vf (7) or log xf = log x' - Af/2.3Vf (7a) Downloaded by guest on September 25, 2021 VOL.
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